Asarinin

Details

• Internal ID: 639d9a8e-8a78-4482-8d45-f574fa10d536
• Taxonomy: Lignans, neolignans and related compounds > Furanoid lignans
• IUPAC Name: 5-[(3R,3aR,6S,6aR)-3-(1,3-benzodioxol-5-yl)-1,3,3a,4,6,6a-hexahydrofuro[3,4-c]furan-6-yl]-1,3-benzodioxole
• SMILES (Canonical): C1C2C(COC2C3=CC4=C(C=C3)OCO4)C(O1)C5=CC6=C(C=C5)OCO6
• SMILES (Isomeric): C1[C@H]2[C@H](CO[C@@H]2C3=CC4=C(C=C3)OCO4)[C@@H](O1)C5=CC6=C(C=C5)OCO6
• InChI: InChI=1S/C20H18O6/c1-3-15-17(25-9-23-15)5-11(1)19-13-7-22-20(14(13)8-21-19)12-2-4-16-18(6-12)26-10-24-16/h1-6,13-14,19-20H,7-10H2/t13-,14-,19-,20+/m0/s1
• InChI Key: PEYUIKBAABKQKQ-WZBLMQSHSA-N
• Popularity: 99 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₀H₁₈O₆
• Molecular Weight: 354.40 g/mol
• Exact Mass: 354.11033829 g/mol
• Topological Polar Surface Area (TPSA): 55.40 Ų
• XlogP: 2.70
• Atomic LogP (AlogP): 3.22
• H-Bond Acceptor: 6
• H-Bond Donor: 0
• Rotatable Bonds: 2

Synonyms

• Asarinin
• l-asarinin
• Episesamin
• 133-03-9
• (+)-Episesamin
• ASARININ (-)
• 1-Asarinine
• AI 3-21202
• (-)-Episesamin
• (-)-ASARININ 97
• Asarinin, (+)-
• UNII-C3RVX72NMG
• UNII-F6PWY73ZGT
• C3RVX72NMG
• F6PWY73ZGT
• 1,3-Benzodioxole, 5,5'-[(1R,3aR,4S,6aR)-tetrahydro-1H,3H-furo[3,4-c]furan-1,4-diyl]bis-, rel-
• NSC 31773
• 5-[(3R,3aR,6S,6aR)-3-(1,3-benzodioxol-5-yl)-1,3,3a,4,6,6a-hexahydrofuro[3,4-c]furan-6-yl]-1,3-benzodioxole
• AI3-00810
• AI3-21202
• 1,3-Benzodioxole, 5,5'-(tetrahydro-1H,3H-furo(3,4-c)furan-1,4-diyl)bis-, (+)-
• l-asarinin/(-)-asarinin
• Isosesamin
• C20H18O6
• D-asarinin
• NSC-31773
• 1,3-BENZODIOXOLE, 5,5'-((1R,3AR,4S,6AR)-TETRAHYDRO-1H,3H-FURO(3,4-C)FURAN-1,4-DIYL)BIS-, REL-
• (+)-Asarinin
• Spectrum_001556
• SpecPlus_000958
• Spectrum2_000811
• Spectrum3_001162
• Spectrum4_001725
• Spectrum5_000490
• BSPBio_002743
• KBioGR_002110
• KBioSS_002036
• MLS002473313
• ASARININ D-FORM [MI]
• CHEMBL43469
• DivK1c_007054
• SCHEMBL976772
• SPECTRUM1504180
• SPBio_000701
• ASARININ DL-FORM [MI]
• MEGxp0_001224
• ASARININ, (+/-)-
• ACon1_000986
• KBio1_001998
• KBio2_002036
• KBio2_004604
• KBio2_007172
• KBio3_002243
• DTXSID201033462
• HMS2223C09
• TNP00112
• BDBM50101976
• CCG-39667
• (-)-Asarinin, >=98% (HPLC)
• AKOS040750231
• SDCCGMLS-0066831.P001
• NCGC00017230-01
• NCGC00169785-01
• NCGC00169785-02
• AS-76837
• SMR001397394
• D85162
• 5,5'-(tetrahydro-1H,3H-furo[3,4-c]furan-1,4-diyl)bis(1,3-benzodioxole)
• (1R,3aR,4S,6aR)-1,4-di(benzo[d][1,3]dioxol-5-yl)hexahydrofuro[3,4-c]furan
• 1,3-BENZODIOXOLE, 5,5'-(TETRAHYDRO-1H,3H-FURO(3,4-C)FURAN-1,4-DIYL)BIS-, (1.ALPHA.,3A.ALPHA.,4.BETA.,6A.ALPHA.)-
• 1,3-Benzodioxole, 5,5'-(tetrahydro-1H,3H-furo(3,4-c)furan-1,4-diyl)bis-, (1alpha,3a alpha,4beta,6a alpha)-
• 1,3-BENZODIOXOLE, 5,5'-(TETRAHYDRO-1H,3H-FURO(3,4-C)FURAN-1,4-DIYL)BIS-, (1S-(1.ALPHA.,3A.ALPHA.,4.BETA.,6A.ALPHA.))-
• 1H,3H-FURO(3,4-C)FURAN, 3A.BETA.,4,6,6A.BETA.-TETRAHYDRO-1.ALPHA.,4.BETA.-BIS(3,4-(METHYLENEDIOXY)PHENYL)-, (+)-
• 5-[(3S,3aR,6R,6aR)-3-(1,3-benzodioxol-5-yl)-1,3,3a,4,6,6a-hexahydrofuro[3,4-c]furan-6-yl]-1,3-benzodioxole
• NCGC00169785-04!5-[(3R,3aR,6S,6aR)-3-(1,3-benzodioxol-5-yl)-1,3,3a,4,6,6a-hexahydrofuro[3,4-c]furan-6-yl]-1,3-benzodioxole

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9915	99.15%
Caco-2	+	0.6230	62.30%
Blood Brain Barrier	+	0.7000	70.00%
Human oral bioavailability	-	0.6714	67.14%
Subcellular localzation	Mitochondria	0.6871	68.71%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9565	95.65%
OATP1B3 inhibitior	+	0.9517	95.17%
MATE1 inhibitior	-	0.8800	88.00%
OCT2 inhibitior	-	0.7750	77.50%
BSEP inhibitior	+	0.8456	84.56%
P-glycoprotein inhibitior	+	0.6624	66.24%
P-glycoprotein substrate	-	0.9820	98.20%
CYP3A4 substrate	-	0.6509	65.09%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.6924	69.24%
CYP3A4 inhibition	+	0.7960	79.60%
CYP2C9 inhibition	+	0.8949	89.49%
CYP2C19 inhibition	+	0.8994	89.94%
CYP2D6 inhibition	+	0.8932	89.32%
CYP1A2 inhibition	+	0.9106	91.06%
CYP2C8 inhibition	-	0.9135	91.35%
CYP inhibitory promiscuity	+	0.9087	90.87%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.8500	85.00%
Carcinogenicity (trinary)	Non-required	0.4507	45.07%
Eye corrosion	-	0.9759	97.59%
Eye irritation	-	0.5861	58.61%
Skin irritation	-	0.6414	64.14%
Skin corrosion	-	0.9410	94.10%
Ames mutagenesis	+	0.6600	66.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.8230	82.30%
Micronuclear	+	0.6300	63.00%
Hepatotoxicity	-	0.5925	59.25%
skin sensitisation	-	0.7600	76.00%
Respiratory toxicity	-	0.5111	51.11%
Reproductive toxicity	+	0.6000	60.00%
Mitochondrial toxicity	-	0.6125	61.25%
Nephrotoxicity	-	0.7034	70.34%
Acute Oral Toxicity (c)	III	0.7553	75.53%
Estrogen receptor binding	+	0.8045	80.45%
Androgen receptor binding	+	0.7777	77.77%
Thyroid receptor binding	+	0.6329	63.29%
Glucocorticoid receptor binding	-	0.5593	55.93%
Aromatase binding	-	0.5000	50.00%
PPAR gamma	+	0.6712	67.12%
Honey bee toxicity	-	0.8459	84.59%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	+	0.5100	51.00%
Fish aquatic toxicity	+	0.9885	98.85%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL3622	P33261	Cytochrome P450 2C19	3162.3 nM	Potency	via CMAUP
CHEMBL3397	P11712	Cytochrome P450 2C9	3981.1 nM	Potency	via CMAUP
CHEMBL289	P10635	Cytochrome P450 2D6	15848.9 nM	Potency	via CMAUP

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	96.55%	91.11%
CHEMBL3137262	O60341	LSD1/CoREST complex	92.50%	97.09%
CHEMBL4481	P35228	Nitric oxide synthase, inducible	91.13%	94.80%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	86.21%	96.77%
CHEMBL2039	P27338	Monoamine oxidase B	85.50%	92.51%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	85.32%	94.45%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	84.76%	95.56%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	83.44%	92.62%
CHEMBL4225	P49760	Dual specificity protein kinase CLK2	83.20%	80.96%
CHEMBL3438	Q05513	Protein kinase C zeta	82.17%	88.48%
CHEMBL1806	P11388	DNA topoisomerase II alpha	81.57%	89.00%
CHEMBL1994	P08235	Mineralocorticoid receptor	81.42%	100.00%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	80.69%	96.09%

Plants that contains it

• Asarum heterotropoides
• Asarum sieboldii
• Cnidoscolus texanus
• Diospyros montana
• Dracaena hanningtonii
• Dryobalanops aromatica
• Eleutherococcus nodiflorus
• Eremophila calorhabdos
• Eremophila phyllopoda
• Flaveria bidentis
• Horsfieldia irya
• Hymenaea oblongifolia
• Knema austrosiamensis
• Lespedeza cyrtobotrya
• Lindera obtusiloba
• Lindera praecox
• Lophocolea bidentata
• Magnolia coco
• Melicope elleryana
• Pilocarpus trachylophus
• Piper mullesua
• Ptelea crenulata
• Quassia bidwillii
• Sesamum indicum
• Teucrium fragile
• Trichilia dregeana
• Uvaria ferruginea
• Veronica anagallis-aquatica
• Virola surinamensis
• Zanthoxylum ailanthoides
• Zanthoxylum armatum
• Zanthoxylum beecheyanum
• Zanthoxylum limoncello
• Zanthoxylum nitidum

Cross-Links

• PubChem: 101612
• NPASS: NPC129687
• ChEMBL: CHEMBL43469
• LOTUS: LTS0230803
• wikiData: Q104394002